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【结 构 式】

【分子编号】30491

【品名】2-Iodoisophthalic acid

【CA登记号】

【 分 子 式 】C8H5IO4

【 分 子 量 】292.02977

【元素组成】C 32.9% H 1.73% I 43.46% O 21.91%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

2-Iodoisophthalic acid (II) is reacted with o-toluidine (I) to give 2-N-(2-methylphenyl)aminoisophthalic acid (III). Cyclization with concentrated H2SO4 provides the 5-methyl-9-oxoacridan-4-carboxylic acid (IV). Conversion of this compound to 5-methyl-9-chloroacridine-4-carbonyl chloride (V) and subsequent selective reaction first with methylamine to provide the methylcarboxamide (VI) and secondly with 4-amino-3-methoxymethanesulfonanilide (VII) gives the hydrochloride salt (VIII) of the desired compound. Conversion via the free base to the isethionate salt provides CI-921.

1 Baguley, B.C.; Denny, W.A.; Finlay, G.J.; Wilson, W.R.; Twigden, S.J.; Atwell, G.J.; Rewcastle, G.W.; Synthesis and antitumour activity and DNA binding properties of a new derivative of amsacrine N,5-dimethyl-9-[(2-methoxy-4-methylsulfonylamino)phenylamino]-4-acridine carboxamide. Cancer Res 1984.
2 Denny, W.A.; Baguley, B.C.; Atwell, G.J.; Potential antitumor agents. 40. Orally active 4,5-disubstituted derivatives of amsacrine. J Med Chem 1984, 27, 3, 363-366.
3 Denny, W.A.; Atwell, G.J.; Baguley, B.C.; CI-921. Drugs Fut 1984, 9, 8, 575.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
13359 2-Hydroxy-1-ethanesulfonic acid 107-36-8 C2H6O4S 详情 详情
(I) 15511 o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine 95-53-4 C7H9N 详情 详情
(II) 30491 2-Iodoisophthalic acid C8H5IO4 详情 详情
(III) 30492 2-(2-toluidino)isophthalic acid C15H13NO4 详情 详情
(IV) 30493 5-methyl-9-oxo-9,10-dihydro-4-acridinecarboxylic acid C15H11NO3 详情 详情
(V) 30494 9-chloro-5-methyl-4-acridinecarbonyl chloride C15H9Cl2NO 详情 详情
(VI) 30495 9-chloro-N,5-dimethyl-4-acridinecarboxamide C16H13ClN2O 详情 详情
(VII) 30496 N-(4-amino-3-methoxyphenyl)methanesulfonamide C8H12N2O3S 详情 详情
(VIII) 30497 9-[2-methoxy-4-[(methylsulfonyl)amino]anilino]-4-methyl-5-[(methylamino)carbonyl]acridinium chloride C24H25ClN4O4S 详情 详情
Extended Information